Sulfuric acid magnesium salt (1:1) → HCID 118468405, compound

HRID 629401Notes

Reaction equation

HRID 629401 reaction equation
[CH:1]([C:3]1[C:12]([CH3:13])=[C:11]([CH3:14])[C:10]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[N:23]=[N:24][N:25]([CH3:27])[CH:26]=3)=[CH:18][CH:17]=2)=[CH:9][C:4]=1[C:5](OC)=[O:6])=[O:2].[O:28]1[CH2:32][CH2:31][CH2:30][C@H:29]1[CH2:33][NH2:34].S([O-])([O-])(=O)=O.[Mg+2]>C1COCC1.C(OCC)(=O)C>[OH:2][CH:1]1[C:3]2[C:4](=[CH:9][C:10]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([C:22]4[N:23]=[N:24][N:25]([CH3:27])[CH:26]=4)=[CH:18][CH:17]=3)=[C:11]([CH3:14])[C:12]=2[CH3:13])[C:5](=[O:6])[N:34]1[CH2:33][C@@H:29]1[CH2:30][CH2:31][CH2:32][O:28]1

Participants

6

Reactant 3

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 641530(S)-(+)-TetrahydrofurfurylamineHCID 118468392HCID 118468392, compound

Product 1

HCID 118468405HCID 118468405, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 2-formyl-3,4-dimethyl-5-(4-(1-methyl-1H-1,2,3-triazol-4-yl)benzyl)benzoate (0.13 g) in THF (3.00 mL) were added 1-((2S)-tetrahydrofuran-2-yl)methanamine (0.04 mL) and anhydrous magnesium sulfate (0.04 g), and the mixture was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate, and the mixture was washed with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (0.11 g).

Workup

  1. washthe mixture was washed with water and saturated brine
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-f5d92e4413604029a4b37054d1f198b2
Source dataset
uspto-grants-2016_04
Patent number
US09315458B2

Reaction notes

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